“I do not approve of your methods.”
“Yeah? Well, you’re not from Chicago.”
Chicago By Night first edition.
This was, I believe, the third book for Vampire: The Masquerade, and it threw the PCs into a city full of interesting monsters. It defined a lot of the Vampire settings as it went - the slick but flawed Prince, the Primogen of elders, mostly but not all representatives of their clans, Sheriff starting as a character before becoming a role, the Tremere being about as messed up as all the other clans, a heap of plot hooks and a handful of odd creatures to play with, the Succubus Club... I could go on, and when V20 came out I considered taking some ideas from here and running Chicago By Night V20 Edition.
If you want to pick up a copy, see above for the PDF on DriveThru. The gateway setting of Gary, Indiana, Forged In Steel is still in the first two editions of the rulebook.
Consider grabbing the collected Chicago Chronicles I PDF which adds the original Succubus Club book for $2.40 extra. Annabelle’s Party is worth the price of admission all by itself.
The City is of Night; perchance of Death
But certainly of Night; for never there
Can come the lucid morning’s fragrant breath
After the dewy dawning’s cold grey air:
The moon and stars may shine with scorn or pity
The sun has never visited that city,
For it dissolveth in the daylight fair.
James Thomson, The City Of Dreadful Night
And Damnation City.
A huge, extensive guide to creating a city setting for a chronicle, some of it Requiem-specific (like what the Princes are and which factions the secret graffiti language refers to) but much of it a great help to Masquerade - or any other game based around the powers that influence a big city, not just in the urban fantasy / horror genres.
To pick just one example, you could drop most of the example Princes into settings in a variety of genres - the Tyrant could seize the throne of a murdered fantasy emperor or the Phantom could be the power behind a thieves’ guild, to pick two radical examples - as well as making quite a few of them the feuding elders of a big city’s vampires.
Pick up the FREE map sections and guide to individualising neighbourhoods while you’re at it.